KR860000258A - Method for producing indole-2-alkanoic acid - Google Patents

Method for producing indole-2-alkanoic acid Download PDF

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KR860000258A
KR860000258A KR1019850004471A KR850004471A KR860000258A KR 860000258 A KR860000258 A KR 860000258A KR 1019850004471 A KR1019850004471 A KR 1019850004471A KR 850004471 A KR850004471 A KR 850004471A KR 860000258 A KR860000258 A KR 860000258A
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methyl
chlorobenzyl
acid
alkyl
indol
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귄던 이반 (외 4)
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재클린 이. 브레버드
머크 프로스트 캐나다 인코포레이티드
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    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom

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Abstract

내용 없음No content

Description

인돌-2-알카노산의 제조방법Method for producing indole-2-alkanoic acid

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (4)

일반식(Ⅱ)의 페닐하이드라진을 일반식(Ⅲ)의 케톤과 반응시킴을 특징으로 하여 일반식(Ⅰa)의 화합물 및 그의 약제학적으로 허용되는 염을 제조하는 방법.A process for preparing a compound of general formula (Ia) and a pharmaceutically acceptable salt thereof, characterized in that phenylhydrazine of general formula (II) is reacted with ketone of general formula (III). 상기식에서, R1은 H 또는 C1내지 C6의 알킬이고;Wherein R 1 is H or C 1 to C 6 alkyl; 이며; ; R8은 각각 독립적으로 H,OH,C1내지 C4-O-알킬, C1내지 C4의 알킬이거나R 8 are each independently H, OH, C 1 to C 4 alkyl, -O-, or alkyl of C 1 to C 4 R1및 R8이 함께 (CH2)V[여기서 V는 1 내지 7의 정수이다] 그룹을 형성하고; R9은 COOR1, CH2OH, CHO, 테트라졸, NHSO2R10, 하이드록시-메틸케톤, CN 또는 CON(R8)2이며;R 1 and R 8 together form a group (CH 2 ) V wherein V is an integer from 1 to 7; R 9 is COOR 1 , CH 2 OH, CHO, tetrazole, NHSO 2 R 10 , hydroxy-methyl ketone, CN or CON (R 8 ) 2 ; R10은 OH, C1내지 C6의 알킬 또는 알콕시, C1내지 C3의 알킬 또는 알콕시그룹, 할로겐, 하이드록시, COOH, CN, 포밀 또는 C1내지 C3의 아실로 치환된 페닐이고; X는 O,S,SO,SO2NR11[여기서, R11은 H, C1내지 C6의 알킬, C1내지 C6의 아실 또는 CN이다],R 10 is phenyl substituted with OH, C 1 to C 6 alkyl or alkoxy, C 1 to C 3 alkyl or alkoxy group, halogen, hydroxy, COOH, CN, formyl or C 1 to C 3 acyl; X is O, S, SO, SO 2 NR 11 wherein R 11 is H, C 1 to C 6 alkyl, C 1 to C 6 acyl or CN, CR1R8또는단위 [여기서, 점선은 임의의 3중 결합을 나타내고, 점선이 3중결합을 나타낼 경우 R1및 R8은 존재하지 않는다]이며;CR 1 R 8 or Unit wherein the dotted line represents any triple bond, and when the dotted line represents a triple bond, R 1 and R 8 do not exist; r 및 q는 각각 독립적으로 0내지 5의 정수이고 p는 0 또는 1인데, 단 p,q 및 r의 합은 2 내지 6이고r and q are each independently an integer of 0 to 5 and p is 0 or 1, provided that the sum of p, q and r is 2 to 6 R1및 R8이 각각 H이고 X가 CH2이며, R4가 5- 메톡시이고 R6가 할로겐이면, p,q 및 r의 합은 3 내지 6이며;When R 1 and R 8 are each H and X is CH 2 , R 4 is 5-methoxy and R 6 is halogen, the sum of p, q and r is 3 to 6; R3는 H,C1내지 C6의 알킬, 페닐, R4로 치환된 페닐, C1내지 C4알킬-페닐 또는 페닐이 R4로 치환된 C1내지 C4알킬페닐이고;R 3 is H, C 1 to C 6 alkyl, phenyl, phenyl substituted with R 4 , C 1 to C 4 alkyl-phenyl or C 1 to C 4 alkylphenyl substituted phenyl with R 4 ; R4,R5,R6및 R7은 각각 독립적으로 (1) 수소, (2) C1내지 C6알킬, (3) C2내지 C6의 알케닐, (4) -(CH2)nM [여기서 n은 0내지3의 정수이고 M은 a)OR12, b)할로겐, c)CF3, d)SR12, e)페닐 또는 하기 R12에서 정의되는 바와 같이 치환된 페닐, f)COO13, Rg)-R14, h)테트라졸, i)-NH--R15, j)-NR13R13, k)-NHSO2R16, l)--CH2OH, m)-SOR12n)-CONR13R13, o)-SO2NR13R13, p)-SO2R12, q) NO2r)O--R14, s)O--NR13R13, t)O--OR15또는 u) CN인데, 여기서 R12는 독립적으로 H, C1내지 C6의 알킬, 벤질 또는 페닐이거나 C1내지 C3의 알킬, 할로겐, CN, CF3, COOR|13, CH2CHOOR13, C1내지 C3의 알콕시 또는 C1내지 C4의 퍼플루오로알킬로 치환된 페닐이고;R 4, R 5, R 6 and R 7 are each independently (1) hydrogen, (2) alkenyl of C 1 to C 6 alkyl, (3) C 2 to C 6, (4) - (CH 2) nM wherein n is an integer from 0 to 3 and M is a) OR 12 , b) halogen, c) CF 3 , d) SR 12 , e) phenyl or phenyl substituted as defined under R 12 , f) COO 13 , Rg) -R 14 , h) tetrazole, i) -NH- -R 15 , j) -NR 13 R 13 , k) -NHSO 2 R 16 , 1) - -CH 2 OH, m) -SOR 12 n) -CONR 13 R 13, o) -SO 2 NR 13 R 13, p) -SO 2 R 12, q) NO 2 r) O- -R 14 , s) O- -NR 13 R 13 , t) O- -OR 15 or u) CN, wherein R 12 is independently H, C 1 -C 6 alkyl, benzyl or phenyl, or C 1 -C 3 alkyl, halogen, CN, CF 3 , COOR | 13 , CH 2 CHOOR 13 , C 1 to C 3 alkoxy or C 1 to C 4 perfluoroalkyl; R13은 독립적으로 H, 페닐, 또는 C1내지 C6의 알킬이며;R 13 is independently H, phenyl, or C 1 to C 6 alkyl; R14는 독립적으로 H, (CH2)nCOOR13(n은 0 내지 4의 정수이다), C1내지 C6의 알킬, CF3, 페틸이거나 R12에서 정의된 바와 같이 치환된 페닐이고;R 14 is independently H, (CH 2 ) n COOR 13 (n is an integer from 0 to 4), C 1 to C 6 alkyl, CF 3 , phenyl, or phenyl substituted as defined for R 12 ; R15는 C1내지 C6의 알킬, 벤질 또는 페닐이며; R16은 C1내지 C6의 알킬, 페닐 또는 CF3이다] 중에서 선택된다.R 15 is C 1 to C 6 alkyl, benzyl or phenyl; R 16 is a C 1 to C 6 alkyl, phenyl or CF 3 a] is selected from. 제1항에 있어서, R1은 H 또는 C1내지 C3의 알킬이고;The method of claim 1, wherein, R 1 is H or C 1 to C 3 alkyl; 이며; ; R8은 각각 독립적으로 H 또는 C1내지 C4의 알킬인데 인돌 질소에 결합된 벤질성 탄소상의 R1은 H이고 R2중의 치환체 R1또는 R8중 적어도 하나는 수소가 아니며;R 8 are each independently H or C 1 to R 1 on the benzylic carbon bonded to the indole nitrogen inde alkyl of C 4 is H, and at least one of the substituents R 1 or R 8 in R 2 is not a hydrogen; R9는 COOH, CH2OH, CHO 또는 테트라졸이고; X는 CR1R8이며;R 9 is COOH, CH 2 OH, CHO or tetrazole; X is CR 1 R 8 is; r 및 q 는 각각 독립적으로 0 내지 3의 정수이고, p는 0 또는 1인데, 단, p,q 및 r의 합은 2 내지 3이고;r and q are each independently an integer of 0 to 3 and p is 0 or 1, provided that the sum of p, q and r is 2 to 3; R3는 C1내지 C6의 알킬인데, 단 시클로알킬은 아니며;R 3 is C 1 to C 6 alkyl, but not cycloalkyl; R4,R5,R6및 R7은 각각 독립적으로 (1) 수소, (2) C1내지 C6의 알킬, (3) a)OR12, b)할로겐, c)CF3, d)SR12, e)-SOR12, f)-SO2R|12, g) O--R14, h)CN,R 4, R 5, R 6 and R 7 are each independently (1) hydrogen, (2) C 1 to C 6 alkyl, (3) a) OR 12, b) halogen, c) CF 3, d) SR 12 , e) -SOR 12 , f) -SO 2 R | 12 , g) O- -R 14 , h) CN, (상기에서, R12는 각기 독립적으로 H, C1내지 C6의 알킬 또는 벤질이고, R14는 H, C1내지 C6의 알킬, CF3또는 페닐이거나 R12에서 정의된 바와 같은 치환된 페닐이다) 중에서 선택되는 일반식(Ⅰa)의 화합물 또는 그의 약제학적으로 허용되는 염을 제조하는 방법.(As in the above, R 12 are each independently an alkyl or benzyl of H, C 1 to C 6, R 14 is substituted as defined in H, C 1 to alkyl, CF 3 or phenyl, or R 12 of C 6 (Ia) or a pharmaceutically acceptable salt thereof. ≪ / RTI > 제1항에 있어서, R1은 H 또는 C1내지 C3의 알킬인데, 단, 인돌 질소에 결합된 벤질성 탄소상의 R1은 H이고;The method of claim 1, wherein, R 1 is inde of H or C 1 to C 3 alkyl, with the proviso that, R 1 on the benzylic carbon bonded to the indole nitrogen is H; R2는 --[-X-]p--R9이며;R 2 is - - [- X-] p - -R < 9 & gt ;; R8은 각각 독립적으로 H 또는 C1내지 C4의 알킬이고;R 8 is each independently an alkyl of H or C 1 to C 4; R9는 COOH, CH2OH, CHO 또는 테트라졸이며; X는 O,S, SO 또는 SO2이고;R 9 is COOH, CH 2 OH, CHO or tetrazole; X is O, S, SO or SO 2 ; r 및 q는 각각 독립적으로 0 내지 3의 정수이고, p는 1인데, 단, p,q 및 r의 합은 2내지 3이며;r and q are each independently an integer of 0 to 3 and p is 1, provided that the sum of p, q and r is 2 to 3; R3은 C1내지 C3의 알킬인데, 단 시클로알킬은 아니고;R 3 is C 1 to C 3 alkyl, but not cycloalkyl; R4,R5,R6및 R7은 각각 독립적으로 (1) 수소, (2) C1내지 C6의 알킬, (3) a)OR12, b)할로겐, c)CF3, d)SR12, e)-SOR12, f)-SO2R|12, g)O--R14, h)CNR 4, R 5, R 6 and R 7 are each independently (1) hydrogen, (2) C 1 to C 6 alkyl, (3) a) OR 12, b) halogen, c) CF 3, d) SR 12 , e) -SOR 12 , f) -SO 2 R | 12 , g) O- -R 14 , h) CN (상기에서 R12는 독립적으로 H, C1내지 C6의 알킬 또는 벤질이고, R14는 H, C1내지 C6의 알킬, CF3, 페닐이거나 R12에서 정의된 바와 같은 치환된 페닐이다) 중에서 선택되는 일반식(Ⅰa)의 화합물 또는 그의 약제학적으로 허용되는 염을 제조하는 방법.Wherein R 12 is independently H, C 1 to C 6 alkyl or benzyl and R 14 is H, C 1 to C 6 alkyl, CF 3 , phenyl or substituted phenyl as defined in R 12 (Ia) or a pharmaceutically acceptable salt thereof. 제1항에 있어서, 3-[1-(P-클로로벤질)-5-클로로-3-메틸-2-인돌릴]-프로피온 산;2. The compound according to claim 1, which is 3- [1- ( P -chlorobenzyl) -5-chloro-3-methyl-2-indolyl] -propionic acid; 3-[1-(P-클로로벤질)-3-메틸-5-플루오로-2-인돌릴]-프로피온 산;3- [1- ( P -Chlorobenzyl) -3-methyl-5-fluoro-2-indolyl] -propionic acid; 3-[1-(P-클로로벤질)-3-메틸-4,6-디클로로-2-인돌릴]-프로피온 산;3- [1- ( P -Chlorobenzyl) -3-methyl-4,6-dichloro-2-indolyl] -propionic acid; 3-[1-(P-클로로벤질)- 3-메틸-4-메톡시-2-인돌릴]-프로피온 산;3- [1- ( P -Chlorobenzyl) -3-methyl-4-methoxy-2-indolyl] -propionic acid; 3-[1-(P-클로로벤질)-3-메틸-6-메톡시-2-인돌릴]-프로피온 산;3- [1- ( P -Chlorobenzyl) -3-methyl-6-methoxy-2-indolyl] -propionic acid; 3-[1-(P-클로로벤질)-3,4-디메틸-2-인돌릴프로피온 산 및3- [1- ( P -chlorobenzyl) -3,4-dimethyl-2-indolylpropionic acid and 3-[1-(P-클로로벤질)-3,6-디메틸-2-인돌릴]-프로피온 산(혼합물);3- [1- ( P -Chlorobenzyl) -3,6-dimethyl-2-indolyl] -propionic acid (mixture); 1-(4-클로로벤질)-3-메틸-5-메톡시-2-(4'-카복시부틸)인돌;1- (4-chlorobenzyl) -3-methyl-5-methoxy-2- (4'-carboxybutyl) indole; 3-[1-(P-클로로벤질)-3,5-디메틸-2- 인돌릴]-프로피온 산;3- [1- ( P -Chlorobenzyl) -3,5-dimethyl-2-indolyl] -propionic acid; 1-(4-클로로벤질)-3-메틸-5-메톡시-2-(3-카복시부틸)인돌;1- (4-chlorobenzyl) -3-methyl-5-methoxy-2- (3-carboxybutyl) indole; 3-[1-(P-클로로벤질)-3-메틸-2- 인돌릴]-프로피온 산;3- [1- ( P -Chlorobenzyl) -3-methyl-2-indolyl] -propionic acid; 3-[1-(P-클로로벤질)-5-브로모-3- 인돌릴]-프로피온 산;3- [1- ( P -Chlorobenzyl) -5-bromo-3-indolyl] -propionic acid; 1-(4-티오메틸벤질)-5-메톡시-3-메틸-2-(2-카복시에틸)인돌;1- (4-thiomethylbenzyl) -5-methoxy-3-methyl-2- (2-carboxyethyl) indole; 1-(4-티오메틸벤질)-5-메톡시-3-메틸-2-(2-카복시에틸)인돌 s-옥사이드;1- (4-thiomethylbenzyl) -5-methoxy-3-methyl-2- (2-carboxyethyl) indole s-oxide; 1-(4-티오메틸벤질)-5-메톡시-3-메틸-2-(3-카복시에틸)인돌;1- (4-thiomethylbenzyl) -5-methoxy-3-methyl-2- (3-carboxyethyl) indole; 4-[1-(P-클로로벤질)-3-메틸-5-플루오로-2-인돌릴]-부타노 산;4- [1- ( P -Chlorobenzyl) -3-methyl-5-fluoro-2-indolyl] -butanoic acid; 3-[1-(P-티오메틸벨질)-3-메틸-5-플루오로-2-인돌릴]프로파노 산;3- [1- ( P -Thiomethylzelli) -3-methyl-5-fluoro-2-indolyl] propanoic acid; 3-[1-(P-메틸설폭시벤질)-3-메틸-5-플루오로-2-인돌릴]-프로파노 산;3- [1- ( P -methylsulfoxybenzyl) -3-methyl-5-fluoro-2-indolyl] -propanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-플루오로-2-인돌릴]부타노 산;3- [1- (4-chlorobenzyl) -3-methyl-5-fluoro-2-indolyl] butanoic acid; 3-메틸-4-[1-(P-클로로벤질-5-메톡시-3-메틸인돌-2-일]부타노 산;3-Methyl-4- [1- ( P -chlorobenzyl-5-methoxy-3-methylindol-2-yl] butanoic acid; 3-메틸-4-[1-(P-클로로벤질-5-플루오로-3-메틸인돌-2-일]부타노 산;3-Methyl-4- [1- ( P -chlorobenzyl) -5-fluoro-3-methylindol-2-yl] butanoic acid; 3-[1-(P-메틸설폭시벤질)-3-메틸-5-메톡시인돌-2-일]-2,2-디메틸프로파노 산;3- [1- ( P -methylsulfoxybenzyl) -3-methyl-5-methoxyindol-2-yl] -2,2-dimethylpropanoic acid; 3-[1-(P-메틸설폭시벤질)-5-하이드록시-3-메틸인돌-2-일]-프로피온 산;3- [1- ( P -methylsulfoxybenzyl) -5-hydroxy-3-methylindol-2-yl] -propionic acid; 3-[1-(P-메틸설폭시벤질)-5-아세톡시-3-메틸인돌-2-일]-프로파노 산;3- [1- ( P -methylsulfoxybenzyl) -5-acetoxy-3-methylindol-2-yl] -propanoic acid; 3-[4,6-디클로로-1-(4-클로로벤질)-3-메틸-1H-인돌-2-일]프로파노 산;3- [4,6-Dichloro-1- (4-chlorobenzyl) -3-methyl-1H-indol-2-yl] propanoic acid; 3-[1-(4-클로로벤질)-4-메톡시-3-메틸-1H-인돌-2-일]-프로파노 산;3- [l- (4-Chlorobenzyl) -4-methoxy-3-methyl-lH-indol-2-yl] -propanoic acid; 2-[1-(4-클로로벤질)-3-메틸-5-플루오로인돌-2-일]-메톡시아세트 산;2- [l- (4-Chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -methoxyacetic acid; 3-[1-(4-브로모벤질)-3- 메틸-5-메톡시인돌-2-일]-2,2-디메틸프로파노 산;3- [1- (4-bromobenzyl) -3-methyl-5-methoxyindol-2-yl] -2,2-dimethylpropanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-메톡시인돌-2-일]-2-메틸-프로파노 산;3- [1- (4-Chlorobenzyl) -3-methyl-5-methoxyindol-2-yl] -2-methyl-propanoic acid; 3-[1-(4-요도벤질)-3-메틸-5-메톡시인돌-2-일]-2,2-디메틸-프로파노 산;3- [1- (4-Iodobenzyl) -3-methyl-5-methoxyindol-2-yl] -2,2-dimethyl-propanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-메톡시인돌-2-일]-2,2-디메틸-프로판올;3- [1- (4-chlorobenzyl) -3-methyl-5-methoxyindol-2-yl] -2,2-dimethyl-propanol; 3-[1-(4-클로로벤질)-3-메틸-5-하이드록시인돌-2-일]-2,2-디메틸-프로파노산;3- [1- (4-Chlorobenzyl) -3-methyl-5-hydroxyindol-2-yl] -2,2-dimethyl-propanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-메톡시인돌-2-일]-프로판올;3- [1- (4-chlorobenzyl) -3-methyl-5-methoxyindol-2-yl] -propanol; 3-[1-(4-클로로벤질)-3-메틸-5-플루오로인돌-2-일]-2,2-디메틸프로파노 산;3- [1- (4-chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -2,2-dimethylpropanoic acid; 3--[1-(4-클로로벤질)-3-메틸-5-플루오로인돌-2-일]-3-메틸프로파노 산;3- [1- (4-chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -3-methylpropanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-하이드록시인돌-2-일]-부타노 산;3- [1- (4-Chlorobenzyl) -3-methyl-5-hydroxyindol-2-yl] -butanoic acid; 메틸4-[1-(4-클로로벤질)-3- 메틸-5-플루오로인돌-2-일]-부타노에이트;Methyl 4- [1- (4-chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -butanoate; 3-[1-(4-클로로벤질)-3-메틸-4-프로필-5-하드록시인돌-2-일]-프로파노 산;3- [1- (4-chlorobenzyl) -3-methyl-4-propyl-5-hydroxyoxyindol-2-yl] -propanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-프로프-2-에녹시인돌-2-일]-프로파노 산;3- [1- (4-Chlorobenzyl) -3-methyl-5-prop-2-enoic acid indol-2-yl] -propanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-메톡시인돌-2-일]-2,2-디메틸-프로파노에이트;3- [1- (4-chlorobenzyl) -3-methyl-5-methoxyindol-2-yl] -2,2-dimethyl-propanoate; 3-[1-(4-클로로벤질)-3-메틸-5-플루오로인돌-2-일]-2-메틸-부타노 산;3- [1- (4-Chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -2-methyl-butanoic acid; 1-(4-클로로벤질)-3-메틸-5-메톡시-1H-인돌-2-메톡시 아세트 산;L- (4-chlorobenzyl) -3-methyl-5-methoxy-lH-indole-2-methoxyacetic acid; 3-[1-(4-클로로벤질)-3-메틸-5-플로로인돌-2-일]-2,2-디메틸-프로파노 산;3- [1- (4-Chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -2,2-dimethyl-propanoic acid; 메틸-3-[1-(4-클로로벤질)-5-메톡시--3-메틸-1H-인돌-2-일]-프로파노에이트;Methyl-3- [l- (4-chlorobenzyl) -5-methoxy-3-methyl-lH-indol-2-yl] -propanoate; 3-[1-(4-아미노벤질)-5-메톡시-3-메틸-1H-인돌-2-일]-2,2-디메틸프로파노 산;3- [1- (4-aminobenzyl) -5-methoxy-3-methyl-1H-indol-2-yl] -2,2-dimethylpropanoic acid; 4-[1-(4-클로로벤질)-5-메톡시-3-메틸-1H-인돌-2-일]-2,2-디메틸부타노 산;4- [1- (4-chlorobenzyl) -5-methoxy-3-methyl-1H-indol-2-yl] -2,2-dimethylbutanoic acid; 4-[1-(4-클로로벤질)-5-플루오로-3-메틸-1H-인돌-2-일]-2,2-디메틸부타노산;4- [1- (4-chlorobenzyl) -5-fluoro-3-methyl-1H-indol-2-yl] -2,2-dimethylbutanoic acid; 4-[1-(4-클로로벤질)-5-하이드록시-3-메틸-1H-인돌-2-일]-3-메틸부타노 산;4- [1- (4-chlorobenzyl) -5-hydroxy-3-methyl-1H-indol-2-yl] -3-methylbutanoic acid; 3-[1-(4-클로로벤질)-5-하이드록시-3-메틸-1H-인돌-2-일]-2,2-디메틸프로파노 산;3- [1- (4-chlorobenzyl) -5-hydroxy-3-methyl-1H-indol-2-yl] -2,2-dimethylpropanoic acid; 3-[1-(4-클로로벤질)-5-하이드록시-3-메틸-1H-인돌-2-일]-3-메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-hydroxy-3-methyl-1H-indol-2-yl] -3-methylpropanoic acid; 3-[1-(4-클로로벤질)-5-에톡시-3-메틸-1H-인돌-2-일]-2,2-디메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-ethoxy-3-methyl-1H-indol-2-yl] -2,2-dimethylpropanoic acid; 4-[1-(4-클로로벤질)-5-플루오로-3-메틸-1H-인돌-2-일]-2,4,3,3-테트라메틸 부타노 산;4- [1- (4-chlorobenzyl) -5-fluoro-3-methyl-1H-indol-2-yl] -2,4,3,3-tetramethylbutanoic acid; 4-[1-(4-클로로벤질)-5-플루오로-3-메틸-1H-인돌-2-일]-4,3,3-트리메틸 부타노 산;4- [1- (4-chlorobenzyl) -5-fluoro-3-methyl-1H-indol-2-yl] -4,3,3-trimethylbutanoic acid; 4-[1-(4-클로로벤질)-5-플루오로-3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 부타노 산;4- [1- (4-chlorobenzyl) -5-fluoro-3-methyl-1H-indol-2-yl] -2,2,3-trimethylbutanoic acid; 4-[1-(4-클로로벤질)-5-플루오로-3-메틸-1H-인돌-2-일]-2,3,3-트리메틸 부타노 산;4- [1- (4-chlorobenzyl) -5-fluoro-3-methyl-1H-indol-2-yl] -2,3,3-trimethylbutanoic acid; 4-[1-(4-클로로벤질)-5-메톡시-3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 부타노 산;4- [1- (4-chlorobenzyl) -5-methoxy-3-methyl-1H-indol-2-yl] -2,2,3-trimethylbutanoic acid; 4-[1-(4-클로로벤질)-5-에톡시-3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 부타노 산;4- [1- (4-chlorobenzyl) -5-ethoxy-3-methyl-1H-indol-2-yl] -2,2,3-trimethylbutanoic acid; 4-[1-(4-클로로벤질)-5-클로로-3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 부타노 산;4- [1- (4-chlorobenzyl) -5-chloro-3-methyl-1H-indol-2-yl] -2,2,3-trimethylbutanoic acid; 4-[1-(4-클로로벤질)-3-메틸-5-트리플루오로메틸-1H-인돌-2-일]-2,4,3,3-테트라메틸 부타노 산;4- [1- (4-chlorobenzyl) -3-methyl-5-trifluoromethyl-lH-indol-2-yl] -2,4,3,3-tetramethylbutanoic acid; 4-[1-(4-클로로벤질)-3-메틸-5-트리플루오로메틸티오-1H-인돌-2-일]-2,4,3,3-테트라메틸 부타노 산;4- [1- (4-chlorobenzyl) -3-methyl-5-trifluoromethylthio-1H-indol-2-yl] -2,4,3,3-tetramethylbutanoic acid; 3-[1-(4-클로로벤질)-5-에톡시-3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-ethoxy-3-methyl-1H-indol-2-yl] -2,2,3-trimethylpropanoic acid; 3-[1-(4-클로로벤질)-5-에톡시-3-메틸-1H-인돌-2-일]-2,3,3-트리메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-ethoxy-3-methyl-1H-indol-2-yl] -2,3,3-trimethylpropanoic acid; 3-[1-(4-클로로벤질)-5-에톡시-3-메틸-1H-인돌-2-일]-2,2,3,3-테트라메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-ethoxy-3-methyl-1H-indol-2-yl] -2,2,3,3-tetramethylpropanoic acid; 3-[1-(4-클로로벤질)-5-메톡시-3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-methoxy-3-methyl-1H-indol-2-yl] -2,2,3-trimethylpropanoic acid; 3-[1-(4-클로로벤질)-5-플루오로-3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-fluoro-3-methyl-1H-indol-2-yl] -2,2,3-trimethylpropanoic acid; 3-[1-(4-클로로벤질)-5-클로로- 3-메틸-1H-인돌-2-일]-2,2,3-트리메틸 프로파노 산;3- [1- (4-chlorobenzyl) -5-chloro-3-methyl-1H-indol-2-yl] -2,2,3-trimethylpropanoic acid; 3-[1-(P-클로로벤질)-3-메틸 -5-메톡시인돌-2-일]-2,2-디에틸 프로파노 산;3- [1- ( P -Chlorobenzyl) -3-methyl-5-methoxyindol-2-yl] -2,2-diethyl propanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-플루오로인돌-2-일]-2,2-디에틸 프로파노 산;3- [1- (4-chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -2,2-diethylpropanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-플루오로인돌-2-일]-2-에틸 프로파노 산;3- [1- (4-chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -2-ethyl propanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-플루오로인돌-2-일]-3-메틸 프로파노 산;3- [1- (4-chlorobenzyl) -3-methyl-5-fluoroindol-2-yl] -3-methylpropanoic acid; 3-[1-(4-클로로벤질)-3-메틸-5-메톡시-2-일]펜타노 산을 제조하는 방법.3- [1- (4-chlorobenzyl) -3-methyl-5-methoxy-2-yl] pentanoic acid. ※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019850004471A 1984-06-25 1985-06-24 Method for producing indole-2-alkanoic acid KR860000258A (en)

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FR2543952B1 (en) * 1982-09-03 1986-02-21 Bristol Myers Co HETEROCYCLIC HYDROCARBON COMPOUNDS BELONGING TO INDOLIC SERIES AND THEIR PHARMACOLOGICAL APPLICATION
GB8607294D0 (en) * 1985-04-17 1986-04-30 Ici America Inc Heterocyclic amide derivatives
US5179112A (en) * 1985-04-17 1993-01-12 Ici Americas Inc. Heterocyclic amide derivatives and pharmaceutical use
DK496086A (en) * 1985-10-17 1987-04-18 Ici America Inc Heterocyclic Compounds
GB8623429D0 (en) * 1985-10-17 1986-11-05 Ici America Inc Carboximide derivatives
GB8707051D0 (en) * 1986-04-15 1987-04-29 Ici America Inc Heterocyclic carboxamides
GB8609175D0 (en) * 1986-04-15 1986-05-21 Ici America Inc Heterocyclic carboxamides
US5081138A (en) * 1986-12-17 1992-01-14 Merck Frosst Canada, Inc. 3-hetero-substituted-n-benzyl-indoles and prevention of leucotriene synthesis therewith
NZ222878A (en) * 1986-12-17 1991-02-26 Merck Frosst Canada Inc 3-hetero-substituted-n-benzyl-indole derivatives, and pharmaceutical compositions
EP0300675A3 (en) * 1987-07-21 1990-04-11 Merck Frosst Canada Inc. Method for the improvement of cyclosporine therapy
DE3807922A1 (en) * 1988-03-10 1989-09-21 Boehringer Mannheim Gmbh SUBSTITUTED HETEROCYCLES, METHOD FOR THE PRODUCTION THEREOF, AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
IT1227362B (en) * 1988-11-18 1991-04-08 Istituto Biochimico Italiano INDOLIC DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS ANTI-THROMBOTIC DRUGS
US5093351A (en) * 1989-01-05 1992-03-03 Du Pont Merck Pharmaceutical Company Substituted indole, benzofuran and benzothiophene derivatives as 5-lipoxygenase inhibitors
NZ234883A (en) * 1989-08-22 1995-01-27 Merck Frosst Canada Inc Quinolin-2-ylmethoxy indole derivatives, preparation and pharmaceutical compositions thereof
US5204344A (en) * 1989-08-22 1993-04-20 Merck Frosst Canada, Inc. (Quinolin-2-ylmethoxy)indoles as inhibitors of the biosynthesis of leukotrienes
US5272145A (en) * 1989-08-22 1993-12-21 Merck Frosst Canada, Inc. (Quinolin-2-ylmethoxy)indoles as inhibitors of the biosynthesis of leukotrienes
GB9108811D0 (en) * 1991-04-24 1991-06-12 Erba Carlo Spa N-imidazolyl derivatives of substituted indole
US5290798A (en) * 1991-09-30 1994-03-01 Merck Frosst Canada, Inc. (hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5389650A (en) * 1991-09-30 1995-02-14 Merck Frosst Canada, Inc. (Azaarylmethoxy)indoles as inhibitors of leukotriene biosynthesis
CA2079374C (en) * 1991-09-30 2003-08-05 Merck Frosst Canada Incorporated (bicyclic-azaarylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5308850A (en) * 1991-09-30 1994-05-03 Merck Frosst Canada, Inc. (Bicyclic-hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5190968A (en) * 1991-09-30 1993-03-02 Merck Frosst Canada, Inc. (Polycyclic-arylmethoxy) indoles as inhibitors of leukotriene biosynthesis
AU3488693A (en) * 1992-02-13 1993-09-03 Merck Frosst Canada Inc. (Azaaromaticalkoxy)indoles as inhibitors of leukotriene biosynthesis
US5374635A (en) * 1993-03-29 1994-12-20 Merck Frosst Canada, Inc. Furo[3,2-b]pyridines and thieno[3,2-b]pyridines as inhibitors of leukotriene biosynthesis
PT802183E (en) * 1996-04-19 2002-03-28 American Home Prod ESTROGENIC AGENTS
US6069153A (en) * 1998-05-12 2000-05-30 American Home Products Corporation Indenoindoles and benzocarbazoles as estrogenic agents
US6479535B1 (en) 1998-05-15 2002-11-12 Wyeth 2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations
GB9902461D0 (en) * 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
US6159959A (en) * 1999-05-06 2000-12-12 American Home Products Corporation Combined estrogen and antiestrogen therapy
US7144913B2 (en) * 2001-05-23 2006-12-05 Merck Frosst Canada & Co. Dihydropyrrolo[1,2-a]indole and tetrahydropyrido[1,2-a]-indole derivatives as prostaglandin d2 receptor antagonists
NZ539406A (en) 2002-10-30 2007-05-31 Merck Frosst Canada Ltd Pyridopyrrolizine and pyridoindolizine derivatives
EA200701504A1 (en) 2005-01-19 2008-02-28 Биолипокс Аб INDOLS SUITABLE FOR THE TREATMENT OF INFLAMMATION
ES2392192T3 (en) 2006-04-24 2012-12-05 Merck Canada Inc. Indole amide derivatives as EP4 receptor antagonists
WO2020003119A1 (en) * 2018-06-25 2020-01-02 Suzhou Mednes Pharma Tech Co., Ltd. Compounds and methods for treatment of hedgehog pathway associated conditions
CN109535060B (en) * 2018-12-20 2022-03-25 苏州麦迪耐斯医药科技有限公司 Hedgehog pathway inhibitor and preparation method and application thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH454858A (en) * 1965-05-13 1968-04-30 Geigy Ag J R Process for the production of new indole derivatives
CH455777A (en) * 1965-05-13 1968-05-15 Geigy Ag J R Process for the production of new indole derivatives

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EP0166591B1 (en) 1989-11-23
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IL75586A (en) 1988-09-30
PT80698A (en) 1985-07-01
JPS6163653A (en) 1986-04-01
ES544524A0 (en) 1986-09-01
ZA854762B (en) 1986-02-26
DK284485D0 (en) 1985-06-24
AU4377685A (en) 1986-01-02
IL75586A0 (en) 1985-10-31
EP0166591A2 (en) 1986-01-02
EP0166591A3 (en) 1986-06-25
DK284485A (en) 1986-02-24
CA1241660A (en) 1988-09-06
ES8609245A1 (en) 1986-09-01
PT80698B (en) 1987-03-31

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